Alakali-metal acetones.



- useful tones, suc

UNITED STATES PATENT OFFICE.

GEORG MERLINQ'O'T'IO CHBZESCIUSKI, AND OTTO PFEFFEB, 0F ELBEBFELD, GERMANY,

assmnons mo s'xnmn'rrc ra'rnn'rs 00. me, or new OF NEW YORK No Drawing.

To all whom it may concern Be it known that we, Gnoae M'namne, professor of chemistr doctor of philoso hy, and .O'rro Cuaznscmsm and O'rro Farm, doctors of philosophy, chemists, citizens of the German Empire, residing at Elberfeld, Germany, have invented new and Improvements in Alkali-Metal Acetones, of which the following is a specification. Y

. We have found that the hitherto unknown technitall as sodium "distinguished by being exceptionally che cally active and are only stable at a low temperature.

In order to illustrate the new process more fully the following example is given, the parts bein by weight: 600 parts of absolute ether are t rown over 40 parts of pulverized sodium amid and the mixture is cooled down to -'20 C. When this temperature is reached 58 parts of dry acetone are slowly added toythe reactionmass, which has to be stirred, care being taken that the temperature does not rise above 15 C. The sodium amid dissolves. After the whole acetone has been added the mixture is still further stirred during one hour and then the ether is distilled off in vac-a0. The sodium acetone remains in the freezing mixture as a colorless crystalline product which is stable only below 0 C., and which decomposes at ordinary room temperatures. With acetylene it forms the hitherto unknown -3-methylbutinol having most probably the formula: CH

cm-ci-czca In order to produce this product in the very valuable alkali metal keacetone having most Q.

' acetylene. In this erature below zero with.

YORK, N. Y., A CORPORATION ALKALI -METAL ACETONES.

Specification of Letters Patent.

Application fled July 7, 1814. Serial No. 849,608.

Patented Jan. 25, 1916.

suspension of sodium acetone in ether a current of acetylene is conducted. The brownish solution is poured into well cooled dilute acetic acid which has to be stirred. The etheral layer contains the B-methylbutinol. It is an almost colorless oil boiling at 105- 106 C In a similar manner other groups, homologous or analogous to the oxyisopropyl group, such as:

H1OB:/6

a can be introduced into hydrocarbons e. g manner 6. g. from ethylmethylketone-sodium and acetylene the 3- methylpentinol CHI n which is an oil boiling at from 120-12l from diethylketone-sodium and acetylene the 3-ethylpentinol CBS-CHI case which is an oil boiling at from 135137 0.; from methylpropylketone-sodium and acetylene the 3-propylbutinol:

CgHr

n-czcn n which is an oil boiling at from 137138 0.; from cyclopenanone-sodium and acetylene the acetylene-carbinol:

CH:'CH|\ m--on| CHrCH C-ECH can be obtained.

Instead of acetylene othcr'hydrocarbons can be used, and instead of acetone other carbonyl-containing bodies a. g, acetic ester, methylethylketone, acetic aldehyde, etc.

We claim v 1. The new alkali metal ketones being colorless crystalline products more or less soluhis in ether and being very chemically active substances by means of which the oxyisopropyl or similar groups can be introduced 1nt0 hydrocarbons, substantially as described.

2. The new sodium acetone having most In testimony whereof we have hereunto probably the formula: set our hands in the presence of two sub- CH, scribing witnesses.

C-0Na 5 cm ggORGclllldERLlNGr. [1,. s.] TO RZESCIUSKI. [L.s.] bem a colorless crystalline compound 1 stabi e only below 0 C., soluble in ether and OTTO PFLIFER being a chemically very active substance; \Vitnesses: forming 3n1ythylbutinol with acetylene, HELEN NUFER,

10 substantially as described. FRANCES N UFER.

2. The new sodium acetone having most probably the formula:

set our hands in the presence of two subscribmg witnesses.

C-ONa 0112 gEoRGMERLlNG. [1,. s.] T'IO HRZESCIUSKI. [L.s.] 138111 a colorless crystalllne compound I 4 stabl e only below 0 (1., soluble in ether and v OTTO PFLIFER' being a chemically very forming 3-1nythylbutino1 10 substantially as described.

Corrections in Letters Patent No. 1,169,341.

active substance WVitnesses: with. acetylene,

I HELEN N UFER,

FRANCES NUFER.

It is hereby certified that in Letters- Patent No.- 1,169,341, granted January 25,

1916, upon the application of Georg .Merling, Otto Chrzesciuski, and Otto Pfefler, V

of Elberfeld, Germany, for an improve'inent Alkali-Metal Acetones, errors appear in the printed specification requiring correction as follows: In the grant and in the printed specification, the naineof the second-mentioned patentee, for Otto Chrzesciuski read Otto Okrzescinslci; page 1, line 92, for the word oyclopenanon'ej read cyclopeatanone; page 2, line 9, elaim 2, for 3-n 1ythylb'utin01 read 8 meth/yZ-- ,butinol; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Oflice. j Signed and sealed this 18th day of April, a 1)., 1916. a

R. Fr WHITEH EAI J,

"Acting Commissioner 61PM.

[sun] In testimony whereof we have hereunto It is hereby certified that in Letters Patent 1%.- 1,169,341, granted January 25, 1916, upon the application of Georg Mel-ling, Otto Chrzesciuski, and Otto Pfefier,

" errors of Elberfeld, Germany, for an improvement in Alkali-Metal Acetones,

appear in the printed specification requiring correction as follows: In the grant and in the printed specification, the name of the second-mentioned patentee, for Otto Chrzesciuski read Otto Uhrzesc'insk'i; page 1, line 92, for the word cyclopenanonei read cyclopentanone; page 2, line 9, claim 2, for 3-mythylbutinol read 3-mefluylbutz'nol; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Oflioe.

Signed and sealed this 18th day of April, A. D., 1916.

R. F: WHITEHEAD,

Acting Commissioner of PM.

[snan] 

